Cocaine addiction is a serious health problem to which there is no uniformly effective medication for its treatment. This disorder has been linked to monoaminergic activity and it is believed that possible therapeutics should target these pathways. Even though sertraline is a well-established serotonin reuptake inhibitor that exists as the cis- isomer, it is less recognized that the trans isomer is also highly potent, but unselective. This study aims to synthesize new analogues of sertraline, in both the cis- and trans- isomeric forms, that will be tested for selectivity against 5-HT, dopamine (DAT), and norepinephrine (NET) binding. The proposed synthetic strategy involves the use of a rhodium catalyzed, C-H insertion/Cope rearrangement-elimination reaction previously developed in the Davies laboratory to rapidly synthesize these analogues. The methodology will then be adapted to a solid phase supported catalyst system for the rapid synthesis of a library of compounds. The data collected from biological testing of these analogues should provide opportunities for the design of medications for the treatment of cocaine addiction. [unreadable] [unreadable] [unreadable]